Senior Director, Strategic Client Success

About the role

This is an exciting career opportunity at a dynamic growth-stage company. In this role, you will lead Headspace's Strategic Client Success group, overseeing a team responsible for our largest and most strategic employer relationships. You will set the vision and operating model for the team, coach and develop high-performing client executives, and partner cross-functionally to drive retention, growth, client outcomes, and long-term strategic value across the portfolio. As a senior leader, you will serve as an executive partner to key customer stakeholders while shaping the strategy, processes, and capabilities that enable the team to consistently deliver measurable business impact.

Responsibilities

• Lead and develop the Strategic Client Success team, fostering a collaborative, high-performing culture by setting performance standards, coaching for excellence, and building bench strength across the team.
• Define and oversee the strategic account planning process across the Strategic Client Success portfolio, ensuring the team develops deep client partnerships that drive long-term value, retention, and growth.
• Own the team’s commercial performance, including renewals, revenue retention, expansion opportunities, utilization based outcomes and proactive risk management, with an emphasis on growing account value over time.
• Serve as the primary point of contact for the CS Center of Excellence, partnering closely with Revenue Operations and Strategy & Operations to build scalable processes, playbooks, and reporting infrastructure across the Strategic Client Success segment.
• Cultivate trusted relationships with key customer C-suite and senior stakeholders, serving as an strategic advisor while coaching the team to deepen executive engagement across the portfolio.
• Strengthen Headspace's consultant and broker strategy by fostering executive relationships with key consultants, brokers, and other third-party partners that influence client success and growth.
• Establish the team’s executive business review strategy and standards, using data-driven insights, ROI metrics, and KPIs to demonstrate value, inform strategy, and guide client decision-making.
• Oversee portfolio health, forecasting, and operational rigor, ensuring accurate account plans, pipeline management, and client data integrity in all appropriate systems, including Salesforce.com.
• Travel to meet with clients (25-30%).

Requirements

• 12+ years of experience in a strategic client-facing role, such as Strategic Account Management, Customer Success, or Relationship Management.
• Experience with Employee Assistance Programs (EAPs) required.
• 3+ years of people leadership experience, including managing client facing Account Executives or Client Success professionals in a fast-paced environment working against revenue and retention targets.
• Proven experience managing a portfolio of large, complex accounts (Fortune 100 companies; 25,000+ employees and/or $1M+ in recurring revenue) including upsell and strategic renewal negotiations.
• Demonstrated track record of consistently meeting or exceeding revenue retention and growth targets.
• Strong business acumen and analytical skills, with the ability to use data to tell a compelling story and demonstrate ROI.
• Deep understanding of the mental health landscape, including industry trends, and payment models.
• Exceptional communication and presentation skills, with the ability to articulate complex concepts and value propositions to a variety of stakeholders, including C-level executives and consultants.
• High emotional intelligence and experience navigating sensitive, high-stakes client conversations with professionalism and strategic insight.
• A confident, proactive self-starter who is comfortable “rolling up their sleeves” to figure things out in a fast-paced, growth environment.

Qualifications

• Experience partnering with Revenue Operations or CS Operations to build scalable processes and reporting.

Skills

• Strategic thinking and execution.
• Client relationship management.
• Account planning and portfolio management.
• Revenue operations and growth strategies.
• Leadership and team development.
• Business acumen and analytics.
• Communication and presentation skills.
• Emotional intelligence and stakeholder management.

Benefits

• Base salary range: $153,990 - $195,000 base + quarterly variable compensation + equity + benefits.
• Comprehensive healthcare coverage.
• Monthly wellness stipend.
• Roth IRA matching.
• Lifetime Headspace membership.
• Generous parental leave.
• Flexible work schedule.

Pay & Schedule

• The anticipated new hire base salary range for this full-time position is $153,990-$195,000 base + quarterly variable compensation + equity + benefits.
• Location: We are currently hiring this role remotely, ideally located near a major city in the US, and Hybrid for San Francisco (SF).
• Candidates must permanently reside in the US full-time.
• For candidates with a primary residence in the greater SF area, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week.

About Headspace

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

Why You’ll Love Working Here

• A mission that matters—with impact you can see and feel.
• A culture that’s collaborative, inclusive, and grounded in our values.
• The chance to shape what mental health care looks like next.
• Competitive pay and benefits that support your whole self.

Additional Information

• Headspace participates in the E-Verify Program.
• Privacy Statement: All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships.